2(3H)-Benzothiazolone, 6-nitro- → 2(3H)-Benzothiazolone, 6-amino-

HRID 1441729Notes

Reaction equation

HRID 1441729 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9](=[O:11])[S:10][C:6]=2[CH:5]=1)([O-])=O>CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9](=[O:11])[S:10][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 6415712(3H)-Benzothiazolone, 6-nitro-

Product 1

HCID 64533292(3H)-Benzothiazolone, 6-amino-Yield 96.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-nitro-2-benzothiazolinone (98 mg, 0.50 mmol) in 20 ml of EtOAc with 10% Pd/C (˜20 mg) was stirred under H2 balloon for 4 h. The reaction mixture was filtered through celite eluting with EtOAc, concentrated under reduced pressure to give 80 mg of 6-amino-2-benzothiazolinone.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washeluting with EtOAc
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-31c2ebe59f674e9cb56caa0268e5f911
Source dataset
uspto-grants-2010_02
Patent number
US07655688B2

Reaction notes

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